EP0315115A3 - 1-acyl-2,3-dihydro-4(1h)-quinolinone-4-oxime derivatives, process for producing them and use thereof - Google Patents

1-acyl-2,3-dihydro-4(1h)-quinolinone-4-oxime derivatives, process for producing them and use thereof Download PDF

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Publication number
EP0315115A3
EP0315115A3 EP19880118167 EP88118167A EP0315115A3 EP 0315115 A3 EP0315115 A3 EP 0315115A3 EP 19880118167 EP19880118167 EP 19880118167 EP 88118167 A EP88118167 A EP 88118167A EP 0315115 A3 EP0315115 A3 EP 0315115A3
Authority
EP
European Patent Office
Prior art keywords
compounds
quinolinone
dihydro
acyl
producing
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
EP19880118167
Other languages
German (de)
French (fr)
Other versions
EP0315115B1 (en
EP0315115A2 (en
Inventor
Ei Mochida
Akio Uemura
Kazuo Kato
Hiroki Tokunaga
Akinori Haga
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Mochida Pharmaceutical Co Ltd
Original Assignee
Hodogaya Chemical Co Ltd
Mochida Pharmaceutical Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hodogaya Chemical Co Ltd, Mochida Pharmaceutical Co Ltd filed Critical Hodogaya Chemical Co Ltd
Publication of EP0315115A2 publication Critical patent/EP0315115A2/en
Publication of EP0315115A3 publication Critical patent/EP0315115A3/en
Application granted granted Critical
Publication of EP0315115B1 publication Critical patent/EP0315115B1/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/10—Antioedematous agents; Diuretics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C07D215/42—Nitrogen atoms attached in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Hematology (AREA)
  • Diabetes (AREA)
  • Obesity (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Quinoline Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

The present invention relates to novel 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime-O-sulfonic acid compounds, (I), processes for producing said compounds, intermediate compounds to produce said compounds and compositions containing said compounds with potent diuretic activity that can be used for treating and/or preventing hypertension, oedema and/or for removing ascites. <CHEM> The present invention is based on the selection of 1-acyl-7-halo-2,3-dihydro-4(1H)-quinolinone-4-oxime-O-sulfonic acid compounds, namely heterocyclic-or fused heterocyclic- carbonyl derivatives at 1 position. The compounds of the present invention containing these substituents have potent hypotensive, anti-oedematous and diuretic effect as well as an activity to remove ascites and are extremely useful for the treatment of diseases and disorders mentioned above.
EP88118167A 1987-10-31 1988-10-31 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives, process for producing them and use thereof Expired - Lifetime EP0315115B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP276474/87 1987-10-31
JP62276474A JP2602037B2 (en) 1987-10-31 1987-10-31 1-acyl-2,3-dihydro-4 (1H) -quinolinone-4-oxime derivatives, process for preparing the same, and pharmaceutical compositions containing diuretic, antihypertensive, anti-edema and ascites removal based on them

Publications (3)

Publication Number Publication Date
EP0315115A2 EP0315115A2 (en) 1989-05-10
EP0315115A3 true EP0315115A3 (en) 1991-02-27
EP0315115B1 EP0315115B1 (en) 1994-06-15

Family

ID=17569953

Family Applications (1)

Application Number Title Priority Date Filing Date
EP88118167A Expired - Lifetime EP0315115B1 (en) 1987-10-31 1988-10-31 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivatives, process for producing them and use thereof

Country Status (8)

Country Link
US (1) US4968680A (en)
EP (1) EP0315115B1 (en)
JP (1) JP2602037B2 (en)
AT (1) ATE107287T1 (en)
AU (1) AU612422B2 (en)
CA (1) CA1339663C (en)
DE (1) DE3850215T2 (en)
ES (1) ES2056873T3 (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW234124B (en) * 1992-07-15 1994-11-11 Sumitomo Chemical Co
WO2005090309A1 (en) * 2004-03-12 2005-09-29 Wyeth 1,2-dihydroquinoline derivatives and method for using the same to treat hiv infection
JP5305704B2 (en) * 2008-03-24 2013-10-02 富士フイルム株式会社 Novel compound, photopolymerizable composition, photopolymerizable composition for color filter, color filter and method for producing the same, solid-state imaging device, and lithographic printing plate precursor
US8889730B2 (en) 2012-04-10 2014-11-18 Pfizer Inc. Indole and indazole compounds that activate AMPK
US9394285B2 (en) 2013-03-15 2016-07-19 Pfizer Inc. Indole and indazole compounds that activate AMPK

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2487346A1 (en) * 1980-07-28 1982-01-29 Hodogaya Chemical Co Ltd 4-OXIMINO-1,2,3,4-TETRAHYDROQUINOLINE DERIVATIVES, PROCESS FOR PREPARING THEM AND THERAPEUTIC APPLICATION THEREOF
EP0163888A1 (en) * 1984-05-05 1985-12-11 Bayer Ag Amidinohydrazones of derivatives of tetraline, chromone, thiachromone, and tetrahydroquinoline, process for their preparation, and their use in medicaments
EP0243982A1 (en) * 1986-05-02 1987-11-04 Mochida Pharmaceutical Co., Ltd. 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivative, process for the production thereof, pharmaceutical composition and intermediates

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4013662A (en) * 1974-12-19 1977-03-22 Pfizer Inc. Alkyl and benzyl 6,7-dialkoxy-2-methyl-4-oxo-1,2,3,4-tetrahydroquinoline-1-carboxylates
US3976650A (en) * 1975-11-04 1976-08-24 Pfizer Inc. Process for preparing optically active 6,7-dimethoxy-2-methyl-4-oxo-1,2,3,4-tetrahydro-1-quinoline carboxylic acid ester analgesics
US4260764A (en) * 1976-12-22 1981-04-07 Pfizer Inc. 9-Hydroxyoctahydrobenzo [C] quinolines and intermediates therefor
US4440770A (en) * 1980-07-28 1984-04-03 Mochida Seiyaku Kabushiki Kaisha Diuretic, hypotensive and antiedemic quinoline oximes
GB2081091B (en) * 1980-07-28 1984-03-07 Mochida Pharm Co Ltd Hypotensive diuretic pharmaceutical compositions containing tetrahydroquinoline derivatives
US4421919A (en) * 1980-07-28 1983-12-20 Hodogaya Chemical Co., Ltd. 4-Oximino-1,2,3,4-tetrahydroquinoline derivatives
US4521607A (en) * 1981-02-27 1985-06-04 Takeda Chemical Industries, Ltd. Chromanyl glycines
PH21213A (en) * 1984-10-26 1987-08-21 Fujisawa Pharmaceutical Co Benzene- and pyrazole- fused heterocyclic compound and pharmaceutical composition comprising the same
DE3660255D1 (en) * 1985-04-12 1988-07-07 Ciba Geigy Ag Oxime sulphonates containing reactive groups
JPH0446951A (en) * 1990-06-14 1992-02-17 Matsushita Electric Works Ltd Phenol resin molding material

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2487346A1 (en) * 1980-07-28 1982-01-29 Hodogaya Chemical Co Ltd 4-OXIMINO-1,2,3,4-TETRAHYDROQUINOLINE DERIVATIVES, PROCESS FOR PREPARING THEM AND THERAPEUTIC APPLICATION THEREOF
EP0163888A1 (en) * 1984-05-05 1985-12-11 Bayer Ag Amidinohydrazones of derivatives of tetraline, chromone, thiachromone, and tetrahydroquinoline, process for their preparation, and their use in medicaments
EP0243982A1 (en) * 1986-05-02 1987-11-04 Mochida Pharmaceutical Co., Ltd. 1-acyl-2,3-dihydro-4(1H)-quinolinone-4-oxime derivative, process for the production thereof, pharmaceutical composition and intermediates

Also Published As

Publication number Publication date
AU2454988A (en) 1989-05-04
EP0315115B1 (en) 1994-06-15
DE3850215D1 (en) 1994-07-21
US4968680A (en) 1990-11-06
ES2056873T3 (en) 1994-10-16
CA1339663C (en) 1998-02-10
EP0315115A2 (en) 1989-05-10
JPH01121269A (en) 1989-05-12
AU612422B2 (en) 1991-07-11
ATE107287T1 (en) 1994-07-15
DE3850215T2 (en) 1994-11-24
JP2602037B2 (en) 1997-04-23

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